Dodecyl amine salt of pentachlorphenol



i033 REtEREItCt.

ttttt X F? 2 9 ,5 2 t3 9 8 I9 23 Patented Uct. 24, 1950 Ficg DODECYL AMINE SALT F PENTACHLORPHENOL Arthur Minich, Westfield, N. L, assignor to 'Nuodex Products, 00., Inc.', Elizabeth, N. J., a

corporation of New York No Drawing. Application May 21, 1946,

Y Serial No. 671,406

This application is a continuation-in-part of application Serial Number 605,188, filed July 14,

1945, which is now abandoned.

This invention is a toxi cant comprising an amine derivative of a halogenated phenol which may be used, according to the present invention, alone, in solution, or as an additive in various compositions or'with an appropriate vehicle to function as a fungicide, bactericide, insecticide, mildewproofing agent, rotproofing agent, disinfectant, germicide, an anti-fouling ingredient of marine paints, and for analogous purposes. It has been found useful in the control or prevention or destruction of a wide variety of micro and macro organisms of plant and animal origin of harmful nature. 7

The compositions of this inventionare produced by reacting together an amine and a halogenated phenol, more particularly an aliphatic amine with an alkyl chain length of 6 to 18 carbon atoms. In practice highly satisfactory results have been obtained by reacting together one or more of the amines with at least one of the halogenated phenols insubstantially stoichiometricalproportions, so as to obtain vphenolates which are substantially. waterinsoluble and substantially oil-soluble.

The reaction maybe and is preferably carried out at temperatures in the range of 150-230 F., although lower temperatures or room temperatures may be satisfactorily employed, The reaction proceeds ,qllite rapidly and a homogeneouscompound is readily formed.

The end roduct may subsequently be dissolved in a suitable solvent, such as. mineral spirits,

1 Claim. (Cl. 260567.5)

xylol, toluol, isophorone, ethylalcohol, butyl alco 3 hol, diacet'one alcohol, and similarorganicjsole vents. It may'also be easily dispersed or diluted with other non-solvent vehicles, such as certain coating material vehicles useful in connection with paints, varnishes, sizings, etc. It has also been found practicable to carry'o'ut the reaction in the presenceof a solvent or non-solvent vehicle or both, so that the endproduct'is formed with either or both the solvent and vehicle and may be used in thisform for-various purposes. It is even possible, in practice, to utilize water as a dispersion vehicle, notwithstanding the end products are not water-soluble. This may be conveniently accomplished by. preparing emulsions and for. such. purpose certain emulsifying agents may be added "to the composition, e. g., petroleumsulphonates. I V, t p

Also the toxicants of this invention may be added to such materials as paraflin wax, aluminum stearate, chlorinated paraflins, casein com positions, leather dressings, etc., to impart toX cantproperties to the resulting composition. The toxicants of this invention have been very thoroughly investigated in the mildewproofing' and preservation of many materials and articles of commerce. For example, these toxicants have been evaluated after introduction into casein paints. Paints of this type are highly susceptible to microbial decomposition during storage and they are also extremely vulnerable to attack by mildew organisms after application to surfaces. Under ordinary conditions of storage, they decompose very rapidly in the containers unless a preservative is present. They will also rapidly succumb to fungus attack after application to surfaces unless a fungicide is present. The toxi-; cants of this invention have been found to possess extreme efficiency in protecting the casein paints during storage as well as after applicationz";

? In evaluation tests'which have been carried out, various percentages of the toxicants were employed and the results were compared with those obtained with other fungicides heretofore commonly available for this purpose. The pres.- ent fungicides proved to be farsuperior to prior toxicants. The amounts of the present toxicants to be employed in such paints depend on the severity of the conditions to be encountered, but generally'a range of from 1% to 10% of the toxis cant per weight of the casein contained inthe paint has been found to be adequate.

The composition is also useful ing other p ggatter similar to casein,, such as those isolated soya bean proteins which 'pr'n; body'the general characteristics of milkc'asein. Good results have also been obtained in connection with the use of the composition: incother paints, such as oil paints, enamels andlacquers. The'toxicants of this invention were also tested in many other compositions, 'includi'ngwcasein leather dressings, house paints, and sizings', and they have shown themselves to behighly'eflicient. The toxicants of this invention mayj be employed to advantage as an insecticide, 'a' con stituent of anti-fouling paints, and in other compositions wherever a toxicant is indicated.

For'the purpose of concrete illustrative dis closure of this invention, the following examples are given;

. 'Ezmmple l 249.1 grams of 2 -bromo- 4-phenylphenol"are mixed with 200 grams of Coconut? amine'la product of Armour and Co., Chicago, Ill.;: consists of a mixture of amines of alkyl chain lengths similar to those of the fatty acids derived from cocoanut oil), at a temperature of 110 F. The reaction is exothermic, and the product, Coconut amine 2-bromo-4-phenylphenolate, is a homogeneous brown crystalline solid, readily solube in mineral spirits, toluene, xylene, ethanol, and most common organic solvents.

Example 2 197.5 grams of 2,4,5-trichlorphenol are mixed with 200 grams of Coconut amine at 180 F. The reaction, when started, is exothermic. The product, Coconut amine 2.4,5-trichlorphenolate, is a liquid that is soluble in mineral spirits, xylol, toluene and ethanol.

Example 3 269 grams of 2,2-dihydroxy-5,5-dichlorodiphenylmethane are mixed with 266 grams of octadecenylamine (a product of Armour 8.: Co., Chicago, 111., consisting of a mixture of chemically pure octadecenyl, hexadecenyl and octadecadienyl amines, having an average molecular weight of 266) and the temperature raised to 180 E. An

exothermic reaction occurs. The product, the mono-octadecenylamine salt of 2,2dihydroxy- 5,5-dichlorodiphenylmethane is a viscous amber liquid, soluble in mineral spirits, toluene, xylene,

benzene, ethanol, and the common organic solvents.

Example 4 269 grams of 2,2-dihydroxy-5-5-dichlorodiphenylmethane are mixed with 297 grams of octa decyldimethyl amine at 180 F. The reaction is mildly exothermic. The product, a viscous amber liquid, consists of the octadecyldimethylamine salt of 2,2'-dihydroxy 5,5-dichlorodiphenyl methane. It is soluble in mineral spirits, toluene, benzene, ethanol, and other common organic solvents.

1 Example 5 266.4 grams of pentachlorphenol is added to'a solution of 200 grams of Coconut amine in 155 grams of ethylene glycol monoethyl ether. The reaction is exothermic. The product is a 75% solution of "Coconut amine pentachlorphenate in ethylene glycol monoethyl ether. This solution is miscible with mineral spirits, toluene, ethanol, and most of the common organic solvents.

Example 7 204 grams of 2-chloro-4-phenylphenol are mixed with 266 grams of octadecenyl amine (from Armour & Co.) at 120 F. The reaction is exothermic. The product, a yellov, crystalline solid, consists of the octadecenylamine salt of 2-chloro- 4-phenylphenol; it is soluble in mineral spirits, toluene, benzene, ethanol, ethylene glycol monoethyl ether and most of the common organic solvents.

Example 8 231.4 grams of 2,3,4,6-tetrachlorphenol are added to a solution of 185 grams of Coconut amine in 139 grams of ethylene glycol monoethyl ether. The reaction is exothermic. The product consists of a solution of -Coconut amine 2,3,4,6-tetrachlorphenolate, and is miscible with mineral spirits, toluene, benzene, ethanol, and most of the common organic solvents.

Example 9 266.4 grams of pentachlorphenol are added to a solution of 266 grams of octadecenyl amine (Armour 8: Co.) in 532 grams of ethanol (anhydrous). The reaction is exothermic. The productconsists of a50% solution of octadecenylamine pentachlorphenate in ethanol. The solution is miscible with mineral spirits, toluene, benzene and other common organic solvents.

Example 10 260 grams of pentachlorphenol are reacted to gether with 185 grams of dodecylamine. This reaction is preferably carried out at elevated temperatures; e. g., about 230 F. Ahomogeneous compound is rapidly formed representing dodecylamine pentachlorphenolate. This end product is soluble in various organic solvents such as xylol, toluol, etc. It is also quite practical to carry out this reaction in the presence of solvents or vehicles so that the end product is formed within the solvent or vehicle.

Example 11 .116 grams of 2,3,4,6tetrachlorphenol and grams of pentachlorphenol are commingled with 185 grams of dodecylamine at room temperature. The reaction is exothermic and the end product is rapidly formed. The multiple amine salt thus prepared is soluble in various organic solvents such as ethylene glycol monoethyl ether, toluol, butyl alcohol, etc.

' Example 12 263 grams of pentachlorphenol are added to 133 grams of octadecenylamine and 92 grams of dodecylamine. Thereis also present 500 grams of amyl alcohol. The reaction proceeds speedily at room. temperature. The end product represents a multiple amine salt in amyl alcohol solution. This solution may be readily diluted further upon the addition of various organic solvents such as mineral spirits, benzol, etc,

Example 13 135 grams of 2,2'-dihydroxy-5,5-dichlorodi phenylmethane together with 125 grams of 2- bromoi-phenylphenol are reacted with 106 grams of cocoanut amine and grams of octadecyldimethylamine. There is also present 600 grams of ethylene glycol monoethyl ether. The reaction is carried out at around F. and proceeds very rapidly. The end product "thus ob tained is a solution of a multiple amine salt. This solution may be readily diluted upon the addition of further quantities of solvents, and it may also be readily incorporated in various vehicles such as varnishes, etc.

The foregoing detailed description sets forth the invention in its preferred practical forms, but the invention is to be understood as fully commensurate with the appended claim.

Having thus fully described the invention, what I claim as new and desire to secure by Letters Patent is:

n-Dodecylammonium pentachlorophenate.

' ARTHUR MINICH.

(R f renc s on following pa UQUQQ IKHLHLIWL oumuu nuuu 6 REFERENCES CITED Number Name Date The following references are of record, in the 21230546 schuler 21, 1942 m of t t 2, 2,97 Coleman Aug. 21, 194:5 2,385,719 Migrdichian Sept. 25, 1945 UNITED. STATES PATENTS 5 2,389,110 Cook Nov. 13, 1945 Number Name Date 2,390,887 Kling Dec. 11, 1945 1,919,298 Lehmann July 25, 1933 2,411,815 SOWa Nov. 26, 1946 2,189,420 Hockenyos Feb. 6, 1940 2,417,809 Coleman Mar. 25, 1947 2,235,629 Clifford 1- Mar. 18, 1941 

